Challenges of Entrepreneurship You Weren’t Warned About

Entrepreneurship is growing. In 2021, 5.5 million small businesses were created, a million more than in 2020 and a 54% increase over 2019.

As basic supply and demand often goes, there has also been an uptick in businesses designed to help entrepreneurs succeed. Which means the digital space is flooded with experts, gurus, and coaches all claiming to help you avoid the challenges of entrepreneurship.

The problem?

Everyone talks about the same challenges with the same solutions.

The financial challenges.

The long hours.

The ups and downs.

Yes, these are all challenges, but they’re also predictable and well known. But what about the challenges you can’t predict? The unexpected challenges of entrepreneurship that can take you by surprise?

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What it Takes to Identify What YOUR Challenges Will Be

Before we list some of the unexpected challenges entrepreneurs face, it’s important to first understand that your challenges are likely to be unique to you.

Nobody is the same. Nobody thinks the same. Nobody operates under the same ideals and principles. No two small businesses are quite the same.

No matter what industry you’re in or what type of business you want to start, you’ll need one skill above all others if you want to make it: self awareness.

You can’t identify challenges if you’re not able to be aware of what’s going wrong in the first place. And most importantly, if you’re the one in charge and running the business, you’re responsible for the challenges at hand.

That means being able to look at yourself and not only ask but also answer the questions:

What am I doing to contribute to this challenge?

How can I best solve this with the resources, people, and time I have at my disposal?

Notice that you don’t have to be the person solving the challenges. But you do have to be the person who can look at them with a separation from yourself and the business.

Don’t do what a lot of failing entrepreneurs do. Don’t make the business a part of your identity. When you fuse your own worth and value—your identity—with the status of the business, your judgment will be clouded. Your ability to identify and solve challenges will be hidden under a veil of ego that will keep you at a disadvantage, especially as your business grows and changes.

Because as your business changes, your challenges change. The only constant will be your own ability to identify, face, and solve them.

This is the challenge you have to face again and again on your journey as an entrepreneur. But it’s certainly not the only one.

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Unexpected Challenges From Real Life Entrepreneurs Still in the Thick of It

Starting a business now is different than it ever was before. While it’s easier in many ways, it’s also more challenging in others. The best people to talk about the unexpected challenges of entrepreneurship are the very people still in the process of solving them.

These eight entrepreneurs from various industries offer insight:

1. Making Decisions That Lead to Happiness at the Expense of Early Growth with Danielle Hope Diamond

The ultimate crux of what it means to be an entrepreneur in 2023 is heading the lessons from our elders. The idea that you have to work a job you hate just to retire and finally get to do the things you love is dying, with many entrepreneurs driving the once-primary ideology farther into the dirt.

Danielle Hope Diamond is one of them, with her digital media company EpiqMedia, where she and her team turn ads into something of the future: videos people actually want to watch and enjoy.

Being a creative business, Diamond says, “Probably the biggest challenge that I had with Epiq in particular first is predictability in the business and especially with a creative business, and then scalability. So predictability wise, especially with the type of work that I slowly realized I wanted to focus on because I could’ve basically gone in a direction that was more entrepreneur-centric where I built out something that was intended to be predictable and scalable and did a bunch of social clips and you know, set it up with a bunch of employees and had it become less creative. But I didn’t want to do that.”

What she chose to create and the direction of her company was the challenge at hand for her.

“That wasn’t making me happy. Those are the things that I did as part of keeping the business going, not the things that I love most about it, and so scalability was a tough learning.”

The solution, or at least the mindset that keeps her business moving forward is the idea that, “sometimes you need those short term quick wins to get you off the ground, but after a certain point, knowing when to not get sucked in by tiny objects and quick wins and focus on the long term stuff that maybe you might not see returns on immediately, but that down the line is really what builds a trusted brand and lasting business and regular very natural lead gen flow.”

2. Determining What to Pay New Hires with Andres Gamboa Barrera

Eventually, your one-person entrepreneur show needs to take on help to grow and thrive. Which means you have to pay someone a salary and more importantly, you have to determine how much to pay that person for their work.

Pay is a fairly common challenge for new business owners. How much do you actually pay someone who’s hired on to help? Where Andres Gamboa Barrera, owner of the podcast Pony Tales as well as a podcast production company, struggles specifically is in knowing what a position is worth both to the business but also for the skillset a new person is bringing to the team.

“The very first thing that comes to mind is trying to determine how much to pay someone to come on board. I’ve been trying my best but sometimes I feel like I over pay and sometimes I feel like I underpay.”

This challenge, much like others in the entrepreneur space, was faced with a lot of advice.

“I was given tips on this. Such as, measure how much time and resources it would take me to do this, value how much that is from a financial standpoint, and then go from there. But even then it’s not as clear or straightforward since the people I’m bringing in have the expertise to do this so it’s less time, or they have a varying availability for it.”

Some employers take to websites that share the “average pay” for certain positions in various parts of the world. But what about if you have a remote business? And what about roles that don’t have a clear title or have varied types of work?

As more and more new skillsets are required for companies nowadays, like video editing, script writing, and other avenues that were once less necessary, the fair pay can be confusing to get right.

As for this entrepreneurship challenge, “I thought it would be easy to solve this puzzle when it came to compensation but it is yet to be clear to me”.

3. Asking for—and Allowing—Support From Others with Candice Storely

Sometimes entrepreneurship takes on a different picture when you’re a one-woman show running a fitness coaching business, online clothing resale shop, and pursuing one-off creative endeavors like custom jackets and canvas paintings.

But these challenges of entrepreneurship are coming up more frequently as individuals decide to take this approach to their own careers. For Candice Storely, her challenge was discovering that, despite being a one-woman show, she didn’t need to go it alone.

“Allowing people to support me and asking for help from people in their areas of genius vs. ‘doing it ALL myself.’ Which, in turn, has created a wonderful network of people, lessons about people, and ultimately growth.”

Asking for help isn’t the challenge itself. It’s allowing the help and support to come, and even admitting when you need it—which can be a challenge for personality types often found in entrepreneurial settings.

“It also plays into the alignment of, as a coach people are asking me for guidance because this is my skill, I need to be that first and foremost and ask for and get support too.”

4. The Creative Energy Needs of Startups with Dillon Barr

Living a life where you get to be creative and make your own decisions is why a lot of people opt for the entrepreneurial life. That’s why Dillon Barr started his company Brudders Beards with butters and balms to help shape and condition your beard.

But while that freedom has its upsides, it also has challenges. We all know that too much of a good thing isn’t always good.

When asked what his biggest challenge has been thus far, it wasn’t the branding or the shipping or even sourcing materials for the all-natural products.

“The consistency of marketing—and creative energy—to ‘keep up’ with the needs of a growing FMCG business. If not the consistency, maybe the strategy.”

While being creative is fun and necessary, most entrepreneurs are doing it all themselves, with little help from others. Even the most creative minds in the world run out of energy at times.

5. Juggling Real Life & Business with Katie Goss

While most entrepreneurs wear the title with pride, it’s not their identity. Meaning they have a real life with hobbies, relaxation, families, and other interests. But, as we’ve already learned, new businesses take time and energy to get off the ground and continue soaring. Katie Goss of Whealth, a wellness brand known for its emphasis on movement and activity being the key to most bodily aches and pains, knows this firsthand.

Her challenges specifically were twofold, fitting given her role as entrepreneur, partner, and mother of two among the many other accolades she possesses.

“As a woman and a mother, none of our responsibilities related to raising our children go away when we become business owners. So there’s this freedom and flexibility that comes with owning your own business, but there’s also this constant struggle for balance between being a mother and a successful businesswoman. Because at the end of the day, my children will ALWAYS come first, but I care deeply about my business, and our members, and its growth is what allows me to be present with my children at every sporting event, school activity, sick day, etc, and it allows me to feel very passionate and fulfilled in my professional life which results in me modeling a level of confidence for my children that I wouldn’t otherwise be able to.”

It’s not easy for everyone to switch hats just because the clock has struck 5pm, especially for women as is evidenced by a higher percentage of mothers leaving entrepreneurship than their counterparts.

“Nobody really talks about the struggle of juggling it all, even when it’s all good stuff. Being a mom to beautiful, healthy boys is a gift I’m eternally grateful for. Owning and operating a business where I can take my struggles in life and use them to help others through difficult times is amazing. Doing what I love with the man I love is incredible. And yet when I’m doing amazing things for my business, I’m often left missing my boys or feeling guilty that I’m not spending that time with them. Conversely, when I’m having an amazing time with my boys, I sometimes feel a hint of guilt that I’m not responding to members quickly enough or doing enough for the business.”

Entrepreneurs care about their businesses. You have to, or you don’t have the stamina to continue through all of these challenges. But that in itself can be a tall mountain to climb when there are other areas of your life that you also care about.

That’s why knowing why you’re doing what you’re doing is important.

6. Removing the Opinion of Others and Recruiting the Right People with Joey Szczepaniak

The sales world has always been around, but it’s growing even more with the influx of businesses with high ticket products like courses or programs. With these businesses come sales reps, hopping on the phone and selling people on why their program is worth thousands.

Joey Szczepaniak is an entrepreneur that coaches this very process and is one of the many who kicked off their business at the tailend of the pandemic. His challenges ranged considerably, but given his industry specifically, one was more difficult.

“Caring about what other people think about me. It’s held me back from making content and really sharing knowledge and value with the world.”

While Szczepaniak has found great success, the challenge of caring too much about what others think may be holding his business back from expanding.

7. Managing an Evolving Landscape in a Sensitive Industry with Brad Snedden

Entrepreneurs in the food industry have it tough. While it’s a great thing that people are caring more about what they’re putting in their body, the natural and whole food space is becoming more competitive, which is especially hard when it comes to sourcing good ingredients.

Brad Snedden, entrepreneur of his protein cookie brand Good Word Foods, voices this challenge specifically.

“Ingredient sourcing is a challenge. When you choose to use ultra-clean ingredients, there tend to be fewer suppliers making them, which gets tricky with growth. You have to be more diligent about working with their production timelines to make sure you can get products.”

If you can’t source ingredients, you can’t create your product, and then do you even have a business? Or just an expensive hobby. These are the challenges entrepreneurs like Snedden face, “because there aren’t a lot of backup options.”

Long-term relationships seem to be the fix here. “Luckily we’ve been working with a lot of the same suppliers for years so we’ve been able to grow together.”

8. Navigating the Myriad of (Unsolicited) Opinions with Sarah Bell

Entrepreneurship looks different when you’re a music artist and creator like Sarah Bell, who hopped on the TikTok train mid-pandemic and went viral with her family-friendly silly songs and messages that teach you not to take yourself too seriously, which she continues now on many platforms and for major brands.

Sometimes, the challenges of entrepreneurship are as simple as knowing how to handle your name.

“A current challenge is growing a platform as a single woman (Sarah Maddack) and then getting married and changing my name to Sarah Bell. I’m currently going by Sarah Maddack Bell now on my platforms, but it doesn’t feel right. I want to change my official brand and artist name to Sarah Bell so I can feel like I’m just one person all the time, but that comes with its own challenges.”

And other times, as a creator on the internet, it’s much harder because everyone has an opinion about everything, even those who wish to be helpful.

“Hearing a million different opinions about what you should be doing to monetize or do creatively. I feel like I’m doing 6 different jobs and guessing my way through all of them, and people are constantly throwing new ideas at me, and it’s just overwhelming.”

Most entrepreneurs have to learn the hard lesson of listening to their gut and doing what they find the most fulfillment in, opinioneers be damned.

9. Internal Resilience and Doing the Work Nobody Sees with With Sam Kraemer

It’s no secret that entrepreneurs are high achievers. It’s what gives them the drive to keep going when the inevitable challenges crop up. Sam Kraemer, owner of a coffee food truck in rural Wisconsin knows this firsthand.

“Through my own personal experiences, and from conversations or group forums, I’ve gathered that there is a problem with the public underestimating the efforts needed to own and operate a successful mobile food and beverage operation. And I know this extends beyond just this industry; having a husband who also owns his own business highlights this problem. And it can be something that we deal with on a daily basis, and it would be easy to get bitter!”

In addition she says, “Doing the work that nobody sees, and that can be underestimated or minimized, and finding your ultimate reason for doing that work so you can overcome the need to prove your worth, or hustle for your worth. That’s been my biggest and unexpected challenge. I’ve built resilience and an understanding for myself that I didn’t realize would come with this business.”

The solution can be even more simple, but often not necessarily easy.

“I’ve had to personally double down on my why: why I love what I do. Why I’m working my ass off. Why I’m tired and at times burnt out, but ultimately fulfilled.”

The business will always have highs and lows. When the lows happen, returning to the reason you’re doing what you do will always help you see the challenges through.

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Running a small business will always come with challenges. It’s best not to run from these challenges, but learn to face them head on. Your challenges will be unique to you, but that just means you will be uniquely equipped to solve them.